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Merck
CN

42073

13-cis-4-Oxoretinoic acid

analytical standard

Synonym(s):

13-cis-4-oxo-RA, 4-Oxoisotretinoin

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About This Item

Empirical Formula (Hill Notation):
C20H26O3
CAS Number:
71748-58-8
Molecular Weight:
314.42
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329756182
MDL number:
MFCD00870452
Beilstein/REAXYS Number:
6067353

Key Documents

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Product Name

13-cis-4-Oxoretinoic acid, analytical standard

InChI

1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13-

SMILES string

CC(/C=C/C1=C(C)C(CCC1(C)C)=O)=C\C=C\C(C)=C(C(O)=O)\[H]

InChI key

GGCUJPCCTQNTJF-FAOQNJJDSA-N

grade

analytical standard

assay

≥98.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical

format

neat

storage temp.

−20°C

Quality Level

100

Application

13-cis-4-Oxoretinoic acid may be used as an analytical standard for the determination of the analyte in biological samples by high performance liquid chromatography (HPLC).

General description

13-cis-4-Oxoretinoic acid, a polar retinoid metabolite that is structurally related to vitamin A, is vital for vision, growth, reproduction and various other physiological functions.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG6837
BCCC1768
BCBV7748

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C Lanvers et al.
Journal of chromatography. B, Biomedical applications, 685(2), 233-240 (1996-10-25)
All-trans-retinoic acid (all-trans-RA) and 13-cis-retinoic acid (13-cis-RA), due to their effects on cell differentiation, proliferation and angiogenesis, improved treatment results in some malignancies. Pharmacokinetic studies of all-trans-RA and 13-cis-RA along with monitoring of retinoic acid metabolites may help to optimize
T Teerlink et al.
Journal of chromatography. B, Biomedical sciences and applications, 694(1), 83-92 (1997-06-20)
A reversed-phase high-performance liquid chromatographic method for the simultaneous analysis of retinol, all-trans-retinoic acid, 13-cis-retinoic acid and 13-cis-4-oxoretinoic acid in human plasma and cell culture medium is described. Sample preparation involves precipitation of proteins and extraction of retinoids with 60%
C Eckhoff et al.
Journal of lipid research, 31(8), 1445-1454 (1990-08-01)
Human plasma was analyzed by high performance liquid chromatography for the presence of retinoic acid and 4-oxoretinoic acid isomers. Peaks that coeluted with the reference compounds all-trans-retinoic acid, 13-cis-retinoic acid, and 13-cis-4-oxoretinoic acid were routinely observed in human plasma. These
C Eckhoff et al.
Biomedical & environmental mass spectrometry, 19(7), 428-433 (1990-07-01)
Eight metabolites of retinol were isolated by high-performance liquid chromatography (HPLC) from the plasma of the non-human primate Macaca fascicularis after acute exposure to 150,000 IU of vitamin A per kilogram body weight. After enrichment and further chromatographic purification, the
Carsten K Schmidt et al.
Analytical biochemistry, 315(1), 36-48 (2003-04-04)
We present a reliable, highly sensitive, and versatile method for the simultaneous determination of endogenous polar (acidic) and apolar (retinol, retinal, and retinyl esters) retinoids in various biological matrices. Following a single liquid extraction of retinoids from tissues or plasma

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